Bakuchiol Explained

Bakuchiol is a meroterpenoid (a chemical compound having a partial terpenoid structure) in the class terpenophenol.[1]

It was first isolated in 1966 by Mehta et al. from Psoralea corylifolia seed and was called Bakuchiol based on the Sanskrit name of the plant, Bakuchi.[2] Bakuchiol is a meroterpene phenol abundant in[3] and mainly obtained from the seeds of the Psoralea corylifolia plant,[4] [5] [6] which is widely used in Indian Ayurveda[7] as well as in Traditional Chinese medicine[8] to treat a variety of diseases.[9] It has also been isolated from other plants, such as P. grandulosa,[10] [11] P. drupaceae,[12] Ulmus davidiana,[13] Otholobium pubescens,[14] Piper longum[15] and Aerva sangulnolenta Blum.

Even though the first complete synthesis of Bakuchiol was described in 1973,[16] its first commercial use in topical applications did not occur until 2007 when it was introduced to the market under the trade name Sytenol A by Sytheon Ltd.

It has been reported to have anticancer activity in preclinical models, possibly due to its structural similarity with resveratrol.[17] One study in rats suggested that Bakuchiol and ethanol extracts of the Chinese medicinal plant Psoralea corylifolia could protect against bone loss.[18]

Bakuchiol possesses antioxidant,[19] [20] anti-inflammatory,[21] [22] and antibacterial[23] properties. Bakuchiol isolated from P. corylifolia has shown activity against numerous Gram-positive and Gram-negative oral pathogens. It was able to inhibit the growth of Streptococcus mutans under a range of sucrose concentrations, pH values and in the presence of organic acids in a temperature-dependent manner and also inhibited the growth of cells adhered to a glass surface.[24]

Despite having no structural resemblance to retinol,[25] Bakuchiol was found to have retinol functionality through retinol-like regulation of gene expression.[26] [27] In 2018, a randomized, double-blind, 12-week clinical study with 44 volunteers demonstrated that Bakuchiol is comparable with retinol in its ability to improve photoaging (wrinkles, hyperpigmentation) but has a better skin tolerance.[28]

Bakuchiol has been found to possess antiandrogenic activity in prostate cancer cells, which inhibited cell proliferation.[29]

See also

External links

Notes and References

  1. Book: J. Elks. The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. C. R. Ganellin. 1990. Springer. 978-1-4757-2085-3. 120–.
  2. Mehta. G.. Nayak. U.Ramdas. Dev. Sukh. January 1966. Bakuchiol, a novel monoterpenoid. Tetrahedron Letters. 7. 38. 4561–4567. 10.1016/s0040-4039(00)70078-5. 0040-4039.
  3. Chaudhuri. R. K.. Bojanowski. K.. Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects. International Journal of Cosmetic Science. 2014 . en. 36. 3. 221–230. 10.1111/ics.12117. 24471735 . 20823803 . subscription.
  4. Banerji . A . Chintalwar . G . Biosynthesis of bakuchiol, a meroterpene from Psoralea corylifolia . Phytochemistry . 22 . 9 . 1983 . 1945–1947 . 10.1016/0031-9422(83)80019-3. 1983PChem..22.1945B .
  5. Cho . Hyun . Jun . Jung-Yang . Song . Eun-Kyoung . Kang . Ki-Hong . Baek . Hum-Young . Ko . Yong-Suk . Kim . Youn-Chul . 3 . Bakuchiol: a hepatoprotective compound of Psoralea corylifolia on tacrine-induced cytotoxicity in Hep G2 cells . Planta Medica . 67 . 8 . 750–751 . 2001 . 10.1055/s-2001-18347 . 11731920 . 260279217 .
  6. Manohar, B. . Divakar, S. . Udaya Sankar, K . Amyloglucosidase Catalyzed Syntheses of Bakuchiol Glycosides in Supercritical Carbon Dioxide . Bulletin of the Korean Chemical Society . 30 . 8 . 2009 . 1760–1766 . 10.5012/bkcs.2009.30.8.1760. free .
  7. https://www.health.harvard.edu/staying-healthy/bakuchiol-does-it-make-skin-look-younger|Bakuchiol: Does it make skin look younger?
  8. Web site: Natural Ingredients - Organic Vegan Non-GMO - Grown Sustainably. 2021-12-22. Plant Mother. en-US.
  9. 30521980. 2019 . Koul . B. . Taak . P. . Kumar . A. . Kumar . A. . Sanyal . I. . Genus Psoralea: A review of the traditional and modern uses, phytochemistry and pharmacology . Journal of Ethnopharmacology . 232 . 201–226 . 10.1016/j.jep.2018.11.036 . 7127090 .
  10. Labbé. Cecilia. Faini. Francesca. Coll. Joseph. Connolly. Joseph D.. July 1996. Bakuchiol derivatives from the leaves of Psoralea glandulosa. Phytochemistry. 42. 5. 1299–1303. 10.1016/0031-9422(96)00144-6. 1996PChem..42.1299L . 0031-9422.
  11. Nadine Backhouse. C. Delporte. Carla L. Negrete. Rosa E. Erazo. Silvia. Zuñiga. Alexandra. Pinto. Alvaro. Cassels. Bruce K. November 2001. Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities. Journal of Ethnopharmacology. 78. 1. 27–31. 10.1016/s0378-8741(01)00309-9. 11585684. 0378-8741.
  12. Lystvan. Kateryna. Belokurova. Valeria. Sheludko. Yuriy. Ingham. John L.. Prykhodko. Valeria. Kishchenko. Olena. Paton. Evgenija. Kuchuk. Mykola. 2009-12-20. Production of bakuchiol by in vitro systems of Psoralea drupacea Bge. Plant Cell, Tissue and Organ Culture. 101. 1. 99–103. 10.1007/s11240-009-9657-0. 10481048. 0167-6857.
  13. Choi. Sang Yoon. Lee. Sanghyun. Choi. Won-Hee. Lee. Yeonmi. Jo. Youn Ock. Ha. Tae-Youl. August 2010. Isolation and Anti-Inflammatory Activity of Bakuchiol from Ulmus davidiana var. japonica. Journal of Medicinal Food. 13. 4. 1019–1023. 10.1089/jmf.2009.1207. 20553183. 1096-620X.
  14. Krenisky . Joann M. . Luo . Jian . Reed . Michael J. . Carney . John R. . 3 . Isolation and Antihyperglycemic Activity of Bakuchiol from Otholobium pubescens (Fabaceae), a Peruvian Medicinal Plant Used for the Treatment of Diabetes. . Biological & Pharmaceutical Bulletin . 22 . 10 . 1999 . 1137–1140 . 10549873 . 10.1248/bpb.22.1137 . free .
  15. Ohno. Osamu. Watabe. Taeko. Nakamura. Kazuhiko. Kawagoshi. Masaru. Uotsu. Nobuo. Chiba. Tomohiro. Yamada. Masayoshi. Yamaguchi. Kohji. Yamada. Kaoru. 2010-07-23. Inhibitory Effects of Bakuchiol, Bavachin, and Isobavachalcone Isolated from Piper longumon Melanin Production in B16 Mouse Melanoma Cells. Bioscience, Biotechnology, and Biochemistry. 74. 7. 1504–1506. 10.1271/bbb.100221. 20622433. 12449051. 0916-8451.
  16. Damodaran. N.P.. Dev. Sukh. January 1973. Meroterpenoids—III. Tetrahedron. 29. 9. 1209–1213. 10.1016/0040-4020(73)80103-6. 0040-4020.
  17. Chen . Zhe . Jin . Ke . Gao . Lingyan . Lou . Guodong . Jin . Ying . Yu . Yongping . Lou . Yijia . 3 . Anti-tumor effects of bakuchiol, an analogue of resveratrol, on human lung adenocarcinoma A549 cell line . European Journal of Pharmacology . 643 . 2–3 . 2010 . 170–9 . 20599920 . 10.1016/j.ejphar.2010.06.025.
  18. Lim . Sun-Hye . Ha . Tae-Youl . Kim . Sung-Ran . Ahn . Jiyun . Park . Hyun Jin . Kim . Suna . 3 . Ethanol extract of Psoralea corylifolia L. and its main constituent, bakuchiol, reduce bone loss in ovariectomised Sprague–Dawley rats . British Journal of Nutrition . 101 . 7 . 2008 . 1031–1039 . 18801207 . 10.1017/S0007114508066750. free .
  19. Adhikari. S.. Joshi. R.. Patro. B. S.. Ghanty. T. K.. Chintalwar. G. J.. Sharma. A.. Chattopadhyay. S.. Mukherjee. T.. September 2003. Antioxidant Activity of Bakuchiol: Experimental Evidences and Theoretical Treatments on the Possible Involvement of the Terpenoid Chain. Chemical Research in Toxicology. 16. 9. 1062–1069. 10.1021/tx034082r. 12971793. 0893-228X.
  20. Haraguchi. Hiroyuki. Inoue. Junji. Tamura. Yukiyoshi. Mizutani. Kenji. 2002. Antioxidative components of Psoralea corylifolia (Leguminosae). Phytotherapy Research. 16. 6. 539–544. 10.1002/ptr.972. 12237811. 27269600. 0951-418X.
  21. Ferrándiz. María Luisa. Gil. Blanca. Sanz. María Jesús. Ubeda. Amalia. Erazo. Silvia. González. Ernesto. Negrete. Rosa. Pacheco. Sergio. Payáa. Miguel. September 1996. Effect of Bakuchiol on Leukocyte Functions and Some Inflammatory Responses in Mice. Journal of Pharmacy and Pharmacology. 48. 9. 975–980. 10.1111/j.2042-7158.1996.tb06016.x. 8910867. 25409612. 0022-3573.
  22. Nadine Backhouse. C. Delporte. Carla L. Negrete. Rosa E. Erazo. Silvia. Zuñiga. Alexandra. Pinto. Alvaro. Cassels. Bruce K. November 2001. Active constituents isolated from Psoralea glandulosa L. with antiinflammatory and antipyretic activities. Journal of Ethnopharmacology. 78. 1. 27–31. 10.1016/s0378-8741(01)00309-9. 11585684. 0378-8741.
  23. Katsura. H.. Tsukiyama. R.-I.. Suzuki. A.. Kobayashi. M.. 2001-11-01. In Vitro Antimicrobial Activities of Bakuchiol against Oral Microorganisms. Antimicrobial Agents and Chemotherapy. 45. 11. 3009–3013. 10.1128/aac.45.11.3009-3013.2001. 11600349. 0066-4804. 90775.
  24. Parimala Devi B, Ramasubramaniaraj R . 2009 . Dental Caries and Medicinal Plants – An Overview . Journal of Pharmacy Research . 2 . 11 . 1669–1675 .
  25. Dhaliwal. S.. Rybak. I.. Ellis. S.R.. Notay. M.. Trivedi. M.. Burney. W.. Vaughn. A.R.. Nguyen. M.. Reiter. P.. Bosanac. S.. Yan. H.. Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing. British Journal of Dermatology. 2019 . en. 180. 2. 289–296. 10.1111/bjd.16918. 29947134 . 49430951 . 0007-0963. free. 2027.42/147746. free.
  26. Chaudhuri RK, Bojanowski K . Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects . International Journal of Cosmetic Science . 36 . 3 . 221–230 . 2014 . 24471735 . 10.1111/ics.12117 . 20823803 .
  27. Chaudhuri. R. K.. Bojanowski. K.. Bakuchiol: a retinol-like functional compound revealed by gene expression profiling and clinically proven to have anti-aging effects. International Journal of Cosmetic Science. 2014 . en. 36. 3. 221–230. 10.1111/ics.12117. 24471735 . 20823803 . subscription.
  28. Dhaliwal. S.. Rybak. I.. Ellis. S.R.. Notay. M.. Trivedi. M.. Burney. W.. Vaughn. A.R.. Nguyen. M.. Reiter. P.. February 2019. Prospective, randomized, double-blind assessment of topical bakuchiol and retinol for facial photoageing. British Journal of Dermatology. 180. 2. 289–296. 10.1111/bjd.16918. 29947134. 0007-0963. free. 2027.42/147746. free.
  29. Miao L. . Ma S . Fan G . etal. 2013 . Bakuchiol inhibits the androgen induced-proliferation of prostate cancer cell line LNCaP through suppression of AR transcription activity . Tianjin Journal of Traditional Chinese Medicine . 30 . 5 . 291–293 . 10.11656/j.issn.1672-1519.2013.05.13 . 2024-02-19 . original title: 补骨脂酚拮抗AR转录活性抑制雄激素诱导的前列腺癌细胞LNCaP的增殖

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